Sodium borohydride → 4-(3-Chloropropoxy)-3-hydroxy-alpha-methylbenzenemethanol

HRID 744223Notes

Reaction equation

[BH4-].[Na+].[Cl:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][C:9]=1[OH:17]>C(O)C.O1CCCC1>[Cl:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:15])[OH:16])=[CH:10][C:9]=1[OH:17]

Participants

Conditions

Temperature: 10 °C

Procedure

To a flask charged with sodium borohydride (1.5 g, 39.4 mmol) under nitrogen and chilled to 10° C. was added, slowly, a solution of 1-[4-(3-chloropropoxy)-3-hydroxyphenyl]ethanone (6.0 g, 26.2 mmol) dissolved in ethanol-tetrahydrofuran (120 ml, 2:1). After total addition, the ice bath was removed and the reaction was stirred at ambient temperature for 3 hours. An additional amount of sodium borohydride (0.2 g, 5.3 mmol) was carefully added. After stirring at ambient temperature for one hour, the solvent was removed in vacuo. The resultant solid residue was diluted with water (100 mi) and left overnight. The product was isolated by vacuum filtration yielding 3.8 g. Two consecutive recrystallizations from toluene provided 3.3 g (55%) of 4-(3-chloropropoxy)-3-hydroxy-α-methylbenzene methanol as a light brown solid, m.p.=107°-109° C.

Workup

additionwas added
additionAfter total addition
customthe ice bath was removed
stirringAfter stirring at ambient temperature for one hour
customthe solvent was removed in vacuo
additionThe resultant solid residue was diluted with water (100 mi)
waitleft overnight
customThe product was isolated by vacuum filtration
customyielding 3.8 g
customTwo consecutive recrystallizations from toluene

Sources & evidence

ORD record: ord-b07c47c3d6b147a69619a87209d55f70
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05559116

Reaction notes

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